114081-08-2Relevant articles and documents
CuCl-catalyzed formation of C-N bond with a soluble base
Feng, Yi-Si,Man, Qiu-Shi,Pan, Pan,Pan, Zong-Qin,Xu, Hua-Jian
, p. 2585 - 2588 (2009)
Tetramethylammonium hydroxide was used as a base instead of a traditional inorganic base in this copper-catalyzed system and some satisfactory results were obtained. Various functional groups were compatible under this reaction condition.
Microwave-assisted organic synthesis: Scale-up of palladium-catalyzed aminations using single-mode and multi-mode microwave equipment
Loones, Kristof T. J.,Maes, Bert U. W.,Rombouts, Geert,Hostyn, Steven,Diels, Gaston
, p. 10338 - 10348 (2005)
Batch wise scale-up of Buchwald-Hartwig aminations under microwave irradiation has been investigated for the first time. Multi-mode (microSYNTH and MARS) (several vessels irradiated in parallel per batch) as well as single-mode (Discover) (one vessel irradiated per batch) platforms can be successfully used for this purpose with trifluoromethylbenzene (benzotrifluoride: BTF) as amination solvent. The obtained yields indicate a direct scalability in BTF for all the studied aminations. The Voyager equipment (based on a Discover platform) is the most convenient system since it allows an automatic continuous batch wise production without the necessity to manually load and unload reaction vessels.
[(PPh3)2NiCl2]-Catalyzed C-N bond formation reaction via borrowing hydrogen strategy: Access to diverse secondary amines and quinolines
Donthireddy,Pandey, Vipin K.,Rit, Arnab
, p. 6994 - 7001 (2021/06/09)
Commercially available [(PPh3)2NiCl2] was found to be an efficient catalyst for the mono-N-alkylation of (hetero)- A romatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine (5b) and mepyramine (5c), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy is also successful in accessing various quinoline derivatives following the acceptorless dehydrogenation pathway.
Synthesis of an Fe-Pd bimetallic catalyst for: N -alkylation of amines with alcohols via a hydrogen auto-transfer methodology
Wu, Peng-Yu,Lu, Guo-Ping,Cai, Chun
, p. 396 - 404 (2021/01/28)
Hydrogen auto-transfer (HAT) or borrowing hydrogen (BH) methodology which combines dehydrogenation, intermediate reaction and hydrogenation, is recognized as an excellent strategy for one-pot synthesis from an economic and environmental point of view. Although much effort has been made on the development of catalysts for HAT reactions, harsh conditions, external base or large amounts of noble metals are still required in most reported catalysis systems, and thus the exploration of a highly efficient and recyclable heterogeneous catalyst remains meaningful. In this work, a novel bimetallic catalyst, Fe10Pd1/NC500 derived from bimetallic MOF NH2-MIL-101(Fe10Pd1), has been prepared, and the catalyst exhibits superior catalytic performance for the N-alkylation of amines with alcohols via a hydrogen auto-transfer methodology. High yields of the desired products were achieved at 120 °C with an alcohol/amine molar ratio of 2?:?1 and required no external additive or solvent. A distinct enhancement in catalytic performance is observed when compared with monometallic catalysts, which can be ascribed to the "synergistic effects"inside the bimetallic alloys. The N-doped carbon support has been revealed to provide the necessary basicity which avoids the requirement of an external base. Moreover, a wide substrate range and remarkable reusability have been shown by Fe10Pd1/NC500, and this work highlights new possibilities for bimetallic catalysts applied in sustainable chemistry.
Water-promoted dehydrative coupling of 2-aminopyridines in heptane: Via a borrowing hydrogen strategy
Azumaya, Isao,Hikawa, Hidemasa,Kikkawa, Shoko,Nakayama, Taku
, p. 23144 - 23150 (2021/07/21)
A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon-nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon-hydrogen bond cleavage was the rate-determining step.
